SK112799A3 - Oxazolidinones, preparation method and use thereof, pharmaceutical compositions - Google Patents
Oxazolidinones, preparation method and use thereof, pharmaceutical compositions Download PDFInfo
- Publication number
- SK112799A3 SK112799A3 SK1127-99A SK112799A SK112799A3 SK 112799 A3 SK112799 A3 SK 112799A3 SK 112799 A SK112799 A SK 112799A SK 112799 A3 SK112799 A3 SK 112799A3
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- indolyl
- oxazolidin
- piperidinylmethyl
- compound
- Prior art date
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- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 239000003814 drug Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 239000005557 antagonist Substances 0.000 claims abstract description 5
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 5
- -1 methylenedioxy group Chemical group 0.000 claims description 48
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
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- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000004310 lactic acid Substances 0.000 description 1
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- 238000004949 mass spectrometry Methods 0.000 description 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- LIJJGMDKVVOEFT-UHFFFAOYSA-N n-benzyl-4-methoxyaniline Chemical compound C1=CC(OC)=CC=C1NCC1=CC=CC=C1 LIJJGMDKVVOEFT-UHFFFAOYSA-N 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
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- 239000012074 organic phase Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- WWPITPSIWMXDPE-UHFFFAOYSA-N para-chloroamphetamine Chemical compound CC(N)CC1=CC=C(Cl)C=C1 WWPITPSIWMXDPE-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- 239000004001 serotonin 1D antagonist Substances 0.000 description 1
- 230000002295 serotoninergic effect Effects 0.000 description 1
- 230000036299 sexual function Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Gynecology & Obstetrics (AREA)
- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Hematology (AREA)
- Anesthesiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19707628A DE19707628A1 (de) | 1997-02-26 | 1997-02-26 | Oxazolidinone |
| PCT/EP1998/000637 WO1998038189A1 (de) | 1997-02-26 | 1998-02-06 | Oxazolidinone als 5-ht2a-antagonisten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK112799A3 true SK112799A3 (en) | 2000-06-12 |
Family
ID=7821498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1127-99A SK112799A3 (en) | 1997-02-26 | 1998-02-06 | Oxazolidinones, preparation method and use thereof, pharmaceutical compositions |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6462056B1 (cs) |
| EP (1) | EP0964863B1 (cs) |
| JP (2) | JP4402175B2 (cs) |
| KR (1) | KR20000075697A (cs) |
| CN (1) | CN1177847C (cs) |
| AR (1) | AR010899A1 (cs) |
| AT (1) | ATE240954T1 (cs) |
| AU (1) | AU739251B2 (cs) |
| BR (1) | BR9807765A (cs) |
| CA (1) | CA2281918C (cs) |
| CZ (1) | CZ299199A3 (cs) |
| DE (2) | DE19707628A1 (cs) |
| DK (1) | DK0964863T3 (cs) |
| ES (1) | ES2197466T3 (cs) |
| HU (1) | HUP0001093A3 (cs) |
| ID (1) | ID22838A (cs) |
| NO (1) | NO313415B1 (cs) |
| PL (1) | PL335100A1 (cs) |
| PT (1) | PT964863E (cs) |
| RU (1) | RU2196140C2 (cs) |
| SK (1) | SK112799A3 (cs) |
| TW (1) | TW531538B (cs) |
| UA (1) | UA58542C2 (cs) |
| WO (1) | WO1998038189A1 (cs) |
| ZA (1) | ZA981579B (cs) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2787328A1 (fr) * | 1998-12-22 | 2000-06-23 | Sanofi Sa | Utilisation d'un antagoniste des recepteurs 5ht2a pour la preparation de medicaments utiles dans le traitement des ronflements et du syndrome de haute resistance ou de resistance des voies aeriennes superieures |
| BR9916618A (pt) * | 1999-01-28 | 2001-10-23 | Bristol Myers Squibb Co | Compostos heterocìclicos antidepressivos |
| ES2165274B1 (es) | 1999-06-04 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de indolilpiperidina como agentes antihistaminicos y antialergicos. |
| CN1158258C (zh) | 1999-06-24 | 2004-07-21 | 东丽株式会社 | 肾上腺素能α1B受体拮抗药 |
| GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
| GB0009803D0 (en) * | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| ES2172436B1 (es) | 2000-10-31 | 2004-01-16 | Almirall Prodesfarma Sa | Derivados de indolilpiperidina como agentes antihistaminicos y antialergicos. |
| ES2268011T3 (es) * | 2001-04-07 | 2007-03-16 | Astrazeneca Ab | Oxazolidinonas que contienen un grupo sulfonimida como antibioticos. |
| PL371335A1 (en) * | 2002-01-22 | 2005-06-13 | Pharmacia & Upjohn Company | Infection-resistant medical devices |
| JPWO2004069828A1 (ja) * | 2003-02-04 | 2006-05-25 | 三菱ウェルファーマ株式会社 | ピペリジン化合物およびその医薬用途 |
| AU2004305563C1 (en) | 2003-12-11 | 2011-07-07 | Sunovion Pharmaceuticals Inc. | Combination of a sedative and a neurotransmitter modulator, and methods for improving sleep quality and treating depression |
| US7157584B2 (en) * | 2004-02-25 | 2007-01-02 | Takeda Pharmaceutical Company Limited | Benzimidazole derivative and use thereof |
| CL2008001002A1 (es) * | 2007-04-11 | 2008-10-17 | Actelion Pharmaceuticals Ltd | Compuestos derivados de oxazolidinona; composicion farmaceutica que comprende a dichos compuestos; y su uso para preparar un medicamento para tratar una infeccion bacteriana. |
| AU2008337096B2 (en) * | 2007-12-18 | 2013-10-17 | Actelion Pharmaceuticals Ltd | 5-aminocyclylmethyl-oxazolidin-2-one derivatives |
| TWI436999B (zh) * | 2008-10-10 | 2014-05-11 | Actelion Pharmaceuticals Ltd | 唑啶基抗生素 |
| WO2014046544A1 (en) | 2012-09-21 | 2014-03-27 | Aapa B.V. | Substituted 3-heteroaryloxy-3-(hetero)aryl-propylamines as serotonin transporter and serotonin ht2c receptor modulators |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3723797A1 (de) * | 1987-07-18 | 1989-01-26 | Merck Patent Gmbh | Oxazolidinone |
| DE4005371A1 (de) * | 1990-02-21 | 1991-08-22 | Merck Patent Gmbh | Oxazolidinone |
| DE4017211A1 (de) * | 1990-05-29 | 1991-12-05 | Merck Patent Gmbh | Oxazolidinone |
| DK152090D0 (da) * | 1990-06-22 | 1990-06-22 | Lundbaek A S H | Piperidylsubstituerede indolderivater |
| DK158590D0 (da) * | 1990-07-02 | 1990-07-02 | Lundbeck & Co As H | Indolderivater |
| TW300895B (cs) * | 1992-07-14 | 1997-03-21 | Nippon Chemiphar Co | |
| DE4324393A1 (de) * | 1993-07-21 | 1995-01-26 | Merck Patent Gmbh | 4-Aryloxy- und 4-Arylthiopiperidinderivate |
| DE4414113A1 (de) * | 1994-04-22 | 1995-10-26 | Merck Patent Gmbh | 3-Indolylpiperidine |
| ZA954689B (en) * | 1994-06-08 | 1996-01-29 | Lundbeck & Co As H | 4-Aryl-1-(indanmethyl dihydrobenzofuranmethyl or dihydrobenzothiophenemethyl) piperidines tetrahydropyridines or piperazines |
| DE19500689A1 (de) * | 1995-01-12 | 1996-07-18 | Merck Patent Gmbh | Indolpiperidin-Derivate |
-
1997
- 1997-02-26 DE DE19707628A patent/DE19707628A1/de not_active Withdrawn
-
1998
- 1998-02-06 DK DK98909397T patent/DK0964863T3/da active
- 1998-02-06 DE DE59808461T patent/DE59808461D1/de not_active Expired - Lifetime
- 1998-02-06 KR KR1019997007764A patent/KR20000075697A/ko not_active Ceased
- 1998-02-06 ES ES98909397T patent/ES2197466T3/es not_active Expired - Lifetime
- 1998-02-06 AT AT98909397T patent/ATE240954T1/de not_active IP Right Cessation
- 1998-02-06 EP EP98909397A patent/EP0964863B1/de not_active Expired - Lifetime
- 1998-02-06 HU HU0001093A patent/HUP0001093A3/hu unknown
- 1998-02-06 RU RU99120183/04A patent/RU2196140C2/ru not_active IP Right Cessation
- 1998-02-06 PL PL98335100A patent/PL335100A1/xx unknown
- 1998-02-06 PT PT98909397T patent/PT964863E/pt unknown
- 1998-02-06 BR BR9807765-1A patent/BR9807765A/pt not_active IP Right Cessation
- 1998-02-06 AU AU63949/98A patent/AU739251B2/en not_active Ceased
- 1998-02-06 WO PCT/EP1998/000637 patent/WO1998038189A1/de not_active Application Discontinuation
- 1998-02-06 CN CNB988028344A patent/CN1177847C/zh not_active Expired - Fee Related
- 1998-02-06 CZ CZ992991A patent/CZ299199A3/cs unknown
- 1998-02-06 CA CA002281918A patent/CA2281918C/en not_active Expired - Fee Related
- 1998-02-06 ID IDW990813D patent/ID22838A/id unknown
- 1998-02-06 JP JP53722398A patent/JP4402175B2/ja not_active Expired - Fee Related
- 1998-02-06 SK SK1127-99A patent/SK112799A3/sk unknown
- 1998-02-06 US US09/380,202 patent/US6462056B1/en not_active Expired - Fee Related
- 1998-02-23 TW TW087102539A patent/TW531538B/zh not_active IP Right Cessation
- 1998-02-25 ZA ZA981579A patent/ZA981579B/xx unknown
- 1998-02-26 AR ARP980100858A patent/AR010899A1/es not_active Application Discontinuation
- 1998-06-02 UA UA99095309A patent/UA58542C2/uk unknown
-
1999
- 1999-08-25 NO NO19994106A patent/NO313415B1/no not_active IP Right Cessation
-
2009
- 2009-06-24 JP JP2009149274A patent/JP2009256363A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PT964863E (pt) | 2003-10-31 |
| WO1998038189A1 (de) | 1998-09-03 |
| JP2001513764A (ja) | 2001-09-04 |
| US6462056B1 (en) | 2002-10-08 |
| HUP0001093A3 (en) | 2001-07-30 |
| KR20000075697A (ko) | 2000-12-26 |
| EP0964863B1 (de) | 2003-05-21 |
| JP2009256363A (ja) | 2009-11-05 |
| TW531538B (en) | 2003-05-11 |
| PL335100A1 (en) | 2000-04-10 |
| DE59808461D1 (de) | 2003-06-26 |
| DE19707628A1 (de) | 1998-08-27 |
| NO313415B1 (no) | 2002-09-30 |
| ES2197466T3 (es) | 2004-01-01 |
| CZ299199A3 (cs) | 1999-11-17 |
| JP4402175B2 (ja) | 2010-01-20 |
| BR9807765A (pt) | 2000-02-22 |
| AR010899A1 (es) | 2000-07-12 |
| AU739251B2 (en) | 2001-10-04 |
| RU2196140C2 (ru) | 2003-01-10 |
| ZA981579B (en) | 1999-03-17 |
| EP0964863A1 (de) | 1999-12-22 |
| HUP0001093A2 (hu) | 2001-06-28 |
| CA2281918C (en) | 2007-04-03 |
| UA58542C2 (uk) | 2003-08-15 |
| ID22838A (id) | 1999-12-09 |
| AU6394998A (en) | 1998-09-18 |
| NO994106D0 (no) | 1999-08-25 |
| CA2281918A1 (en) | 1998-09-03 |
| CN1248973A (zh) | 2000-03-29 |
| NO994106L (no) | 1999-10-19 |
| DK0964863T3 (da) | 2003-08-04 |
| CN1177847C (zh) | 2004-12-01 |
| ATE240954T1 (de) | 2003-06-15 |
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